Stereoselective synthesis of α-C-substituted 1,4-dideoxy-1 4-imino-D-galactitols.: Toward original UDP-Galf mimics via cross-metathesis

被引：35

作者：

Liautard, V ^{[1
]}

Desvergnes, V ^{[1
]}

Martin, OR ^{[1
]}

机构：

[1] Univ Orleans, CNRS, Inst Chim Organ & Analyt, UMR 6005, F-45067 Orleans 2, France

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 07期

关键词：

D O I：

10.1021/ol053078z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Various alpha-C-substituted 1,4-dideoxy-1,4-imino-D-galactitols were prepared efficiently from 1-O-acetyl-2,3,5,6-tetra-O-benzyl-D-glucofuranose by a four-step sequence involving as the key step the highly syn-selective TMSOTf-catalyzed addition of silylated nucleophiles to a glycofuranosylamine. Cross-metathesis of the alpha-C-allylated iminogalactofuranose derivative with an original uridin-5'-yl vinylphosphonate led to novel UDP-galactofuranose mimics. Such compounds are of interest as potential inhibitors of the mycobacterial galactan biosynthesis pathway.

引用

页码：1299 / 1302

页数：4

共 41 条

[1] Identification and partial characterization of two eukaryotic UDP-galactopyranose mutases [J].

Bakker, H ;

Kleczka, B ;

Gerardy-Schahn, R ;

Routier, FH .

BIOLOGICAL CHEMISTRY, 2005, 386 (07) :657-661

[2] Enzymatic synthesis of UDP-(3-deoxy-3-fluoro)-D-galactose and UDP-(2-deoxy-2-fluoro)-D-galactose and substrate activity with UDP-galactopyranose mutase [J].

Barlow, JN ;

Blanchard, JS .

CARBOHYDRATE RESEARCH, 2000, 328 (04) :473-480

[3] Positional isotope exchange catalyzed by UDP-galactopyranose mutase [J].

Barlow, JN ;

Girvin, ME ;

Blanchard, JS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (29) :6968-6969

[4] Crystal structures of Mycobacteria tuberculosis and Klebsiella pneumoniae UDP-galactopyranose mutase in the oxidised state and Klebsiella pneumoniae UDP-galactopyranose mutase in the (Active) reduced state [J].

Beis, K ;

Srikannathasan, V ;

Liu, H ;

Fullerton, SWB ;

Bamford, VA ;

Sanders, DAR ;

Whitfield, C ;

McNeil, MR ;

Naismith, JH .

JOURNAL OF MOLECULAR BIOLOGY, 2005, 348 (04) :971-982

[5] Eukaryotic UDP-galactopyranose mutase (GLF gene) in microbial and metazoal pathogens [J].

Beverley, SM ;

Owens, KL ;

Showalter, M ;

Griffith, CL ;

Doering, TL ;

Jones, VC ;

McNeil, MR .

EUKARYOTIC CELL, 2005, 4 (06) :1147-1154

[6] New concise total synthesis of (+)-lentiginosine and some structural analogues [J].

Cardona, F ;

Moreno, G ;

Guarna, F ;

Vogel, P ;

Schuetz, C ;

Merino, P ;

Goti, A .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (16) :6552-6555

[7]

CHRISTINA A, UNPUB

[8] SYNTHESIS OF AZASUGARS BY GRIGNARD REACTION ON GLYCOSYLAMINES [J].

CIPOLLA, L ;

LAY, L ;

NICOTRA, F ;

PANGRAZIO, C ;

PANZA, L .

TETRAHEDRON, 1995, 51 (16) :4679-4690

[9] Chiral oxime ethers in asymmetric synthesis.: Part 7 -: O-(1-phenylbutyl)benzyloxyacetaldoxime, a versatile reagent for the asymmetric synthesis of protected 1,2-aminoalcohols, α-amino acid derivatives, and 2-hydroxymethyl nitrogen heterocycles including iminosugars [J].

Cooper, TS ;

Larigo, AS ;

Laurent, P ;

Moody, CJ ;

Takle, AK .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (07) :1252-1262

[10] A rapid synthesis of hexofuranose-like iminosugars using ring-closing metathesis [J].

Cren, S ;

Wilson, C ;

Thomas, NR .

ORGANIC LETTERS, 2005, 7 (16) :3521-3523

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